Generally…no they don’t test that. Many of the old/superseded patches will prevent themselves from installing over a newer version, returning the message ‘This patch is not applicable to your system’.
The right way to patch superseded vulnerabilities is actually to apply the latest version of the patch that supersedes the older one.
Enabling ‘Evaluate superseded content’ is generally done for reporting fidelity - so you can use a tool like BigFix Compliance to report “how many months out of date” for the system. Remediation usually means applying current patches.